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Ring‐Opening Reactions of Cyclopropenedicarboxylates with Organolithiums and Organozincs
Author(s) -
Liu Yu,
Yu Qiong,
Ma Shengming
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201588
Subject(s) - chemistry , ring (chemistry) , moiety , reagent , cyclopropene , bromide , medicinal chemistry , leaving group , polymer chemistry , organic chemistry , catalysis
Ring‐opening reactions of cyclopropenedicarboxylates with organolithiums and organozincs have been studied. Organolithiums and dialkyl‐ or diphenylzincs afforded a series of 1‐alkenyl malonates with attack occurring by the organic group from the organometallic reagent at the less substituted sp 2 ‐hybridized carbon of the cyclopropene moiety. Mechanistic studies proved both anion and dianion intermediates are involved in the reactions with organolithiums. Phenylcyclopropenedicarboxylate and phenylzinc bromide underwent a ring‐opening dimerization to afford a 1,4‐enyne product.